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The main stories usually involve more research, so I imagine they’re prepared well in advance. But it’ll probably get covered in one of the shorter segments preceding the main story that pad out the running time (those don’t make it on the official YouTube but I think they’re more topical).
He looks and acts exactly like my AP Spanish teacher down to the specific solid but identifably American accent
edit: when I searched YouTube for a clip of ¡Jeb! speaking Spanish I came across a Jimmy Kimmel clip from 2021 titled “President George W. Bush Plays ‘Bushism Or Not?’”…the existence of such a segment is enough of a cognitohazard that I can’t conscionably link it. You already know exactly what the comments look like.